I too suffered from Analysis Paralysis (See my first blog post http://www.biggerpockets.com/blogs/5070-tips-and-tricks-for-buy-and-hold-investors) Go find a good property and buy it!

You are the cause of your own ongoing suffering here.

I guess it's harder to quantify the damage a tenant suffers from a missed appointment, whereas if a tenant misses an appointment and the technician send me a bill for the missed appointment, I have something actionable and can forward it to the tenant for reimbursement.That said, if one of my tenants waited around for a long time for a no-show technician, I would probably offer some type of compensation, depending on the circumstance - even if the tenant didn't request it.

When is it a good time to take legal action for rent not paid. Is it a certain dollar amount or maybe when you don’t want the reputation of being the one that lets tenants go on rent not paid. Recently had a roommate ...

Cash flow is great on STR however I did suffer some setbacks when covid hit but the market is bouncing back.   

There are other issues that can come up besides what you might think you want to do with real property (life estate as you said) and bank accounts (POD as you said); your father could begin to suffer from diminished capacity and might need a guardianship or DPOA at some point in the future, there are advanced directives, POLST forms, benefits planning... 

As a result of the aforementioned acts, Plaintiff and Class members lost money or property and suffered injury in fact.100.

Medical Payments: Provides coverage for an injury suffered on the premises.

If the property suffered loss and the insurance was used, expect the rates to be more.

My father’s business suffers from the same symptoms that many small businesses face in that a lot of its success is based on the fact that he does everything himself.